AU2016286804B2 - Oral solid formulation containing irinotecan and method of preparing the same - Google Patents
Oral solid formulation containing irinotecan and method of preparing the same Download PDFInfo
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- AU2016286804B2 AU2016286804B2 AU2016286804A AU2016286804A AU2016286804B2 AU 2016286804 B2 AU2016286804 B2 AU 2016286804B2 AU 2016286804 A AU2016286804 A AU 2016286804A AU 2016286804 A AU2016286804 A AU 2016286804A AU 2016286804 B2 AU2016286804 B2 AU 2016286804B2
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- AU
- Australia
- Prior art keywords
- acid
- solid formulation
- oral solid
- irinotecan
- acidifying agent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 92
- 238000009472 formulation Methods 0.000 title claims abstract description 74
- 239000007787 solid Substances 0.000 title claims abstract description 71
- 229960004768 irinotecan Drugs 0.000 title claims abstract description 51
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 29
- 239000002535 acidifier Substances 0.000 claims abstract description 45
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 239000004480 active ingredient Substances 0.000 claims abstract description 16
- 239000008187 granular material Substances 0.000 claims description 32
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 239000007884 disintegrant Substances 0.000 claims description 16
- 238000007922 dissolution test Methods 0.000 claims description 15
- 239000011230 binding agent Substances 0.000 claims description 13
- 238000002156 mixing Methods 0.000 claims description 13
- 239000003085 diluting agent Substances 0.000 claims description 12
- 238000004090 dissolution Methods 0.000 claims description 12
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
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- GURKHSYORGJETM-WAQYZQTGSA-N irinotecan hydrochloride (anhydrous) Chemical compound Cl.C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 GURKHSYORGJETM-WAQYZQTGSA-N 0.000 description 46
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- 238000012360 testing method Methods 0.000 description 9
- -1 inorganic acid salt Chemical class 0.000 description 8
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 5
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| AU2021204259A AU2021204259A1 (en) | 2015-06-30 | 2021-06-23 | Oral solid formulation containing irinotecan and method of preparing the same |
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| KR10-2015-0093413 | 2015-06-30 | ||
| KR1020150093413A KR102293907B1 (ko) | 2015-06-30 | 2015-06-30 | 이리노테칸 함유 경구용 고형제제 및 그 제조방법 |
| PCT/KR2016/006513 WO2017003120A1 (en) | 2015-06-30 | 2016-06-20 | Oral solid formulation containing irinotecan and method of preparing the same |
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| KR102293907B1 (ko) * | 2015-06-30 | 2021-08-26 | 한미약품 주식회사 | 이리노테칸 함유 경구용 고형제제 및 그 제조방법 |
| KR102066402B1 (ko) * | 2017-12-22 | 2020-01-15 | 대화제약 주식회사 | 이리노테칸 또는 그의 약제학적으로 허용가능한 염을 포함하는 경구투여용 약제학적 조성물 |
| KR102185475B1 (ko) * | 2019-06-20 | 2020-12-02 | 대화제약 주식회사 | 이리노테칸 자유 염기를 포함하는 경구투여용 약학 조성물 |
| KR102444073B1 (ko) * | 2020-01-06 | 2022-09-16 | (주)휴온스 | 안정성이 향상된 메틸에르고메트린말레산염 함유 약제학적 제제 및 이의 제조방법 |
| KR20220006776A (ko) * | 2020-07-09 | 2022-01-18 | 주식회사유한양행 | 다이아미노피리미딘 유도체 또는 이의 약학적으로 허용가능한 염을 포함하는 약학 조성물 및 이의 제조방법 |
| EP4193987A1 (en) * | 2020-08-06 | 2023-06-14 | SK Biopharmaceuticals Co., Ltd. | Solid oral composition comprising carbamate compound, and preparation method therefor |
| TW202233593A (zh) | 2020-10-07 | 2022-09-01 | 美商亞瑟尼克斯公司 | 乙醯胺基－苯基四唑衍生物及其使用方法 |
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| US6881420B2 (en) * | 2000-06-23 | 2005-04-19 | Teva Pharmaceutical Industries Ltd. | Compositions and dosage forms for gastric delivery of irinotecan and methods of treatment that use it to inhibit cancer cell proliferation |
| US20070299099A1 (en) * | 2004-10-01 | 2007-12-27 | Kabushiki Kaisha Yakult Honsha | Acid Addition Salt of Irinotecan |
| WO2015107131A1 (en) * | 2014-01-17 | 2015-07-23 | Oncoral Pharma Aps | Solid oral dosage form of irinotecan for the treatment of cancer |
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| JPS6019790A (ja) | 1983-07-14 | 1985-01-31 | Yakult Honsha Co Ltd | 新規なカンプトテシン誘導体 |
| IL134592A0 (en) | 1998-06-18 | 2001-04-30 | Univ George Washington | Compositions comprising camptothecin compounds for the treatment of cancer with reduced side effects |
| GB9925127D0 (en) | 1999-10-22 | 1999-12-22 | Pharmacia & Upjohn Spa | Oral formulations for anti-tumor compounds |
| JP2002154963A (ja) | 2000-11-14 | 2002-05-28 | Yakult Honsha Co Ltd | 徐放性抗腫瘍剤 |
| US6476068B1 (en) * | 2001-12-06 | 2002-11-05 | Pharmacia Italia, S.P.A. | Platinum derivative pharmaceutical formulations |
| PL372318A1 (en) | 2002-03-01 | 2005-07-11 | Pharmacia Italia S.P.A. | Crystalline polymorphic form of irinotecan hydrochloride |
| US20060030578A1 (en) | 2002-08-20 | 2006-02-09 | Neopharm, Inc. | Pharmaceutically active lipid based formulation of irinotecan |
| JP4245384B2 (ja) | 2003-03-18 | 2009-03-25 | 株式会社ヤクルト本社 | カンプトテシン類含有医薬組成物 |
| US20050208146A1 (en) | 2003-10-30 | 2005-09-22 | Pfizer Inc | Novel dosage and administration method for oral camptosar |
| CA2588445C (en) | 2004-12-03 | 2013-06-25 | Merck & Co., Inc. | Pharmaceutical formulation containing a release rate controlling composition |
| KR101368519B1 (ko) | 2005-05-23 | 2014-02-27 | 노파르티스 아게 | 결정형 및 기타 형태의 4-아미노-5-플루오로-3-［6-(4-메틸피페라진-1-일)-1ｈ-벤즈이미다졸-2-일］-1ｈ-퀴놀린-2-온 락트산염 |
| CN101283983A (zh) | 2007-10-26 | 2008-10-15 | 南京长澳医药科技有限公司 | 一种稳定的喜树碱类药物脂质体组合物 |
| US7880591B2 (en) | 2008-02-01 | 2011-02-01 | Apple Inc. | Consumer abuse detection system and method |
| EP2153821A1 (en) | 2008-08-06 | 2010-02-17 | BioAlliance Pharma | Oral formulations of camptothecin derivatives |
| CN102617584B (zh) | 2012-03-14 | 2013-10-16 | 海南锦瑞制药股份有限公司 | 一种盐酸伊立替康化合物及其药物组合物 |
| IL266415B2 (en) | 2012-11-30 | 2024-03-01 | Glaxosmithkline Llc | Innovative pharmaceutical composition |
| KR102293907B1 (ko) * | 2015-06-30 | 2021-08-26 | 한미약품 주식회사 | 이리노테칸 함유 경구용 고형제제 및 그 제조방법 |
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| US6881420B2 (en) * | 2000-06-23 | 2005-04-19 | Teva Pharmaceutical Industries Ltd. | Compositions and dosage forms for gastric delivery of irinotecan and methods of treatment that use it to inhibit cancer cell proliferation |
| US20070299099A1 (en) * | 2004-10-01 | 2007-12-27 | Kabushiki Kaisha Yakult Honsha | Acid Addition Salt of Irinotecan |
| WO2015107131A1 (en) * | 2014-01-17 | 2015-07-23 | Oncoral Pharma Aps | Solid oral dosage form of irinotecan for the treatment of cancer |
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